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Synlett 1991; 1991(3): 151-153
DOI: 10.1055/s-1991-20658
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Diastereoselective Preparation of Cyclopropane Amino Acids: Synthesis of Norcoronamic Acid

Anne Gaucher* , Jean Ollivier, Jacques Salaün
  • *Laboratoire des Carbocycles, associé au C.N.R.S., Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, F-91405 Orsay, France
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Publication Date:
07 March 2002 (online)

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The 2-(benzylamino)-4-chlorobutyronitrile (3b), resulting from the addition of benzylamine to the cyanohydrin 2 (4-chloro-2-hydroxybutyronitrile), undergoes Swern N-oxidation followed by quantitative base-induced cyclization to provide the 1-aminocyclopropanecarboxylic acid (ACC) precursor 5d (1-benzylideneaminocyclopropanecarbonitrile). Analogously prepared from the chiral ß-hydroxyester 7 [(S)-(+)-methyl 3-hydroxy-2-methylpropionate], the nitrile amines 10a,b [2-(benzylamino)-4-chloro-3-methylbutyronitrile] undergo Swern N-oxidation and diastereoselective cyclization leading readily to the natural Norcoronamic acid [6; (1S,2S)-1-amino-2-methylcyclopropanecarboxylic acid (ds>84%)].